1,5-Dihydroxynaphthalene

Base Information

• Chemical Name: 1,5-Dihydroxynaphthalene
• CAS No.: 83-56-7
• Deprecated CAS: 1013361-23-3
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 29072900
• European Community (EC) Number: 201-487-4
• ICSC Number: 1604
• NSC Number: 7202
• UNII: P25HC23VH6
• DSSTox Substance ID: DTXSID2052574
• Nikkaji Number: J70.174B
• Wikipedia: 1,5-Dihydroxynaphthalene
• Wikidata: Q19842073
• ChEMBL ID: CHEMBL204658
• Mol file: 83-56-7.mol

Synonyms:1,5-dihydroxynaphthalene

Chemical Property of 1,5-Dihydroxynaphthalene

Chemical Property:

• Appearance/Colour: gray powder
• Vapor Pressure: 3.62E-06mmHg at 25°C
• Melting Point: 259-261 °C (dec.)(lit.)
• Refractive Index: 1.725
• Boiling Point: 375.4 °C at 760 mmHg
• PKA: 9.28±0.40(Predicted)
• Flash Point: 193.5 °C
• PSA: 40.46000
• Density: 1.33 g/cm³
• LogP: 2.25100
• Storage Temp.: 2-8°C
• Solubility.: 0.6g/l
• Water Solubility.: Soluble in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

1,5-Dihydroxynaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, Xi
• Hazard Codes: Xn,N,Xi
• Statements: 22-51/53-36-36/37/38
• Safety Statements: 22-24/25-61-39-29-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Naphthols
• Canonical SMILES: C1=CC2=C(C=CC=C2O)C(=C1)O
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes.
• Uses: 1,5-Dihydroxynaphthalene is an intermediate of synthetic mordant azo dyes. It is an intermediate used in organic synthesis, pharmaceuticals, dyestuff fields and photograph industry.

Technology Process of 1,5-Dihydroxynaphthalene

There total 27 articles about 1,5-Dihydroxynaphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

1,5-dimethoxynaphthalene (10075-63-5) → 5-methoxynaphthalen-1-ol (3588-80-5) + 1,5-dihydroxynaphthalene (83-56-7)

Guidance literature:

With Cyclohexyl iodide; In N,N-dimethyl-formamide; for 2.5h; Heating;

DOI:10.1016/j.tetlet.2008.04.070

Reference yield: 40.0%

1,5-diacetoxynaphthalene (605-89-0) → 1,5-dihydroxynaphthalene (83-56-7) + 5-hydroxynaphthalen-1-yl acetate (94807-85-9)

Guidance literature:

With lipase of Pseudomonas sp; water; In various solvent(s); at 25 ℃; for 2.5h;

DOI:10.1016/S0040-4020(99)01000-5

Reference yield: 25.5%

α-naphthol (90-15-3) → 1,7-Dihydroxynaphthalene (575-38-2) + 1,5-dihydroxynaphthalene (83-56-7)

Guidance literature:

With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride; at -20 ℃; for 0.5h; Mechanism; Product distribution;

DOI:10.1016/S0040-4039(00)88105-8

upstream raw materials:

5-amino-1-naphthol

1-hydroxynaphthalene-5-sulphonic acid

1-aminonaphthalene-5-sulfonic acid

naphthalene-1,5-disulfonate

Downstream raw materials:

7-hydroxy-4-methyl-benzo[h]chromen-2-one

2-(1,5-dihydroxy-[2]naphthoyl)-benzoic acid

2,2'-(1,5-dihydroxy-naphthalene-2,6-dicarbonyl)-di-benzoic acid

1,5-Bis-trimethylsilyloxy-naphthalin

Refernces

Asymmetric Total Synthesis of PD-116740

10.1021/acs.orglett.0c03990

The study presents an asymmetric total synthesis of (+)-PD-116740, an angucyclinone with potent anticancer activity. The synthesis involved a convergent approach with naphthalene-1,5-diol as the starting material, which was converted into quinone derivatives and then reduced to hydroquinone. Selective protection and bromination steps led to the formation of coupling precursors. The D ring fragment was prepared from benzyl alcohol, with TBS protection, lithium/bromide exchange, and conversion to an alkyne. A Pd-catalyzed Suzuki-Miyama coupling reaction combined the A/B and D ring fragments. Asymmetric dihydroxylation using osmium tetroxide and a chiral ligand introduced chirality. The core trans-9,10-dihydrophenanthrene-9,10-diol unit was constructed via oxidative cyclization using Cu(OH)OTf·NMI2 as the oxidant, which also facilitated phenol oxidation. Finally, global deprotection yielded PD-116740.

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